Coniferyl alcohol

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Structural formula
Structural formula of coniferol
General
Surname Coniferyl alcohol
other names
  • 4 - [( E ) -3-hydroxyprop-1-enyl] -2-methoxyphenol
  • 3 - [( E ) -4-Hydroxy-3-methoxyphenyl] -2-propen-1-ol
  • 4-hydroxy-3-methoxy-cinnamon alcohol
Molecular formula C 10 H 12 O 3
Brief description

colorless prisms

External identifiers / databases
CAS number 458-35-5
EC number 207-277-9
ECHA InfoCard 100.006.617
PubChem 1549095
ChemSpider 1266063
Wikidata Q418993
properties
Molar mass 180.20 g mol −1
Physical state

firmly

Melting point

73-74 ° C

boiling point

163-165 ° C (400 Pa )

solubility
safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Coniferyl alcohol is a phenylpropanoid . It is the aglycon of coniferin and a component of softwood - lignin .

Extraction

Theodor Hartig was first able to characterize it in 1861 in the cambial sap of the larch. The Holzminden pharmacist Wilhelm Kubel identified the glucoside of coniferyl alcohol in 1866. It was first obtained in 1874 by F. Tiemann and W. Haarmann by acid hydrolysis of the glucoside coniferin or today by the enzyme emulsin (a β- glucosidase ).

biochemistry

Coniferyl alcohol is a metabolic intermediate in the biosynthesis of eugenol .

Individual evidence

  1. a b c d e f Entry on coniferyl alcohol. In: Römpp Online . Georg Thieme Verlag, accessed on December 28, 2014.
  2. Entry on coniferyl alcohol in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  3. Data sheet Coniferyl alcohol, 98% at AlfaAesar, accessed on February 9, 2019 ( PDF )(JavaScript required) .
  4. W. Kubel: Coniferin - a glucoside from the cambial sap of the conifers . In: Journal für Praktische Chemie 97 , 243-246 (1866). doi : 10.1002 / prac.18660970132 .
  5. F. Tiemann, W. Haarmann: About coniferin and its transformation into the aromatic principle of vanilla . In: Reports of the German Chemical Society 7 , 608–623 (1874). doi : 10.1002 / cber.187400701193 . Digitized on Gallica .